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Identification
YMDB IDYMDB00656
NameD-glucitol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSorbitol (glucitol) is a six-carbon sugar alcohol found in apples, pears, peaches, and prunes. It is synthesized by sorbitol-6-phosphate dehydrogenase, and converted to fructose by succinate dehydrogenase and sorbitol dehydrogenase. Succinate dehydrogenase is an enzyme complex that participates in the citric acid cycle.
Structure
Thumb
Synonyms
  • (-)-Sorbitol
  • (2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
  • 1,2,3,4,5,6-Hexanehexol
  • Cholaxine
  • clucitol
  • Cystosol
  • D-(-)-Sorbitol
  • D-1,2,3,4,5,6-hexanehexol
  • d-Galactitol
  • D-Glucitol
  • d-sorbit
  • d-Sorbite
  • D-Sorbitol
  • D-Sorbol
  • Diakarmon
  • Esasorb
  • Glucarine
  • glucitol
  • Glucitol, D-
  • gulitol
  • Hexahydric alcohol
  • Hexitol
  • Karion
  • l-gulitol
  • Multitol
  • Nivitin
  • Orbit
  • Probilagol
  • Resulax
  • Sionit
  • Sionit K
  • Sionite
  • Sionon
  • Siosan
  • Sorban
  • Sorbelite C
  • Sorbicolan
  • Sorbilande
  • Sorbilax
  • sorbite
  • Sorbitol
  • Sorbitur
  • Sorbo
  • Sorbol
  • Sorbostryl
  • Sorbostyl
  • Sorvilande
CAS number50-70-4
WeightAverage: 182.1718
Monoisotopic: 182.07903818
InChI KeyInChIKey=FBPFZTCFMRRESA-JGWLITMVSA-N
InChIInChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1
IUPAC Name(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
Traditional IUPAC NameD-sorbitol
Chemical FormulaC6H14O6
SMILESOC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAldehydes
Sub ClassBeta Ketoaldehydes
Other Descriptors
  • Organic Oxonium Compounds
Substituents
  • Organic Oxonium Compounds
Physical Properties
StateLiquid
Charge0
Melting point11 °C
Experimental Properties
PropertyValueReference
Water Solubility2750 mg/mL at 30 oC [MULLIN,JW (1972)]PhysProp
LogP-2.20 [SANGSTER (1994)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility229.0ALOGPS
logP-2.7ALOGPS
logP-3.7ChemAxon
logS0.1ALOGPS
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.4 m3·mol-1ChemAxon
Polarizability17.01 Å3ChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Pathways
  • Fructose and mannose metabolism ‐ 00051
  • Galactose metabolism ‐ 00052
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Sarthy, A. V., Schopp, C., Idler, K. B. (1994). "Cloning and sequence determination of the gene encoding sorbitol dehydrogenase from Saccharomyces cerevisiae." Gene 140:121-126.8125328
Synthesis Reference:Liu, Haichao; Luo, Chen. Method for manufacturing sorbitol and mannitol with cellulose. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 8pp.
External Links:
ResourceLink
CHEBI ID:17924
HMDB ID:HMDB00247
Pubchem Compound ID:5780
Kegg ID:C00794
ChemSpider ID:24533858
Wikipedia:Sorbitol
BioCyc ID:SORBITOL

Enzymes

General function:
Involved in zinc ion binding
Specific function:
L-iditol + NAD(+) = L-sorbose + NADH
Gene Name:
SOR1
Uniprot ID:
P35497
Molecular weight:
38165.39844
Reactions
L-iditol + NAD(+) = L-sorbose + NADH.
General function:
Involved in oxidoreductase activity
Specific function:
Reduces the cytotoxic compound methylglyoxal (MG) to (R)-lactaldehyde similar to GRE2. MG is synthesized via a bypath of glycolysis from dihydroxyacetone phosphate and is believed to play a role in cell cycle regulation and stress adaptation. In pentose-fermenting yeasts, aldose reductase catalyzes the reduction of xylose into xylitol. The purified enzyme catalyzes this reaction, but the inability of S.cerevisiae to grow on xylose as sole carbon source indicates that the physiological function is more likely methylglyoxal reduction
Gene Name:
GRE3
Uniprot ID:
P38715
Molecular weight:
37118.5
Reactions
Alditol + NAD(P)(+) = aldose + NAD(P)H.
(R)-lactaldehyde + NADP(+) = methylglyoxal + NADPH.